For four years, something called XOXO has happened. XOXO is deceptively difficult to describe. From the outside it looks like a somewhat unconventional, but still pretty understandable, art and technology convention in Portland, Oregon.

If I had only one sentence to explain what I thought XOXO was to a person, I would have said “Two guys named Andy from the Internet started a low-key gathering of independent creators to share their perspectives on creating things for the Internet.”

As an experimental event, every XOXO has had some form of the following disclaimer:

“XOXO is an experimental event, we don’t know if we’re going to do this again, but if there is anything we can do better over the course of these few days then let us know.”

I have no idea how much of it has actually been the same event each year. Somehow even with that disclaimer, XOXO happens. As a result of that disclaimer though, XOXO has transformed into something different from what I had come to expect from a “tech conference.”

The presenters this year shared stories about taking risks and putting your work into the world, about letting yourself be vulnerable and building empathy, and about some of the most deeply personal and difficult times in their lives and how they overcame them.

Heather Armstrong spoke about her career on the Internet, making a living sharing her experiences as a mother. As ad revenue shrank, sponsored content became the primary way that her and other mothers blogging on the Internet could continue to remain independent voices. An independent voice is inherently incompatible with sponsored content. Her sponsors, seemingly unaware of who they had sent on a sponsored trip to generate sponsored content, tried to have her “take it down immediately and make it disappear.” You can’t do that on the Internet. She shared the consequences of that sponsored content. She talked about her last piece, a tearful, forced family trip sanitized of any unpleasantness, her realization that her children had been written into her contract, and that she wanted to leave that way of making a living on the Internet behind.

Mallory Ortberg talked about her experience starting The Toast and how “there is room for taking risks that aren’t completely outrageous and out of nowhere.” C. Spike Trotman spoke about finding a sustainable level of success on the Internet and then helping others to do the same. Their message to all of us was, “there is room for you to do it too.”

Kathy Sierra taught us what she learned from trying to teach other people and help them overcome their obstacles and motivate them through their real-life challenges that most other technical books aren’t designed for. A short recipe for an amazing book. One key ingredient: Make your user feel like a badass.

Amit Gupta, of Photojojo, shared his story of learning that he was going to die, how he overcame his chances of survival, and his realization after that not only did he want to quit working at Photojojo, the company of his dreams that he had started, he wanted to be absolutely inessential to its continued existence. Over the months following his recovery, he made himself completely unnecessary and sold the company. He asked us to close our eyes and imagine that we learned we were going to die, and then to imagine three things we would regret. Then he asked is if we could start one of those three things when we get back from XOXO, just one thing, “What would it be?” Then he asked us to turn to the person next to us and tell them that one thing, our biggest regret that we were going to start to correct once we got home, back from this surreal experience and into our lives.

By the end of Amit’s talk I had been crying for nearly an hour next to three people I had just met, sharing the one thing we would regret if we learned we were going to die and endlessly encouraging each other with “YOU’RE A BADASS!” and recursively replying “NO YOU ARE!”

With the above speakers, it would be a very unusual lineup for a tech conference, but XOXO isn’t really a tech conference.

This tweet by Andy McMillan, one of the two* Andys behind the conference, explains the difference best.

If I had only one sentence to explain what I thought XOXO was to a person now, I would say, “Two guys named Andy from the Internet started the biggest group therapy session ever or something. At least the year I went.”

This year’s XOXO was a great experience. I can’t quite explain how it was exactly what I needed in so many ways, but all of XOXO is that little push you need to get out there and try something new. I hope that there is another XOXO and I hope that I am fortunate enough to be able to attend. In the first year of XOXO, Anil Dash shared detailed descriptions of the speakers’ talks in the spirit of what he called the “Joy of Missing Out.” As someone paying attention to XOXO from afar, I was thankful for his effort. In the years since, with the talks eventually ending up on YouTube, that kind of sharing of the XOXO experience isn’t as necessary.

In the spirit of XOXO’s ephemerality and the Andys’ instructions to us this year to “make it our own,” I’m going to take the time to process and share what I learned there from my perspective. Links to the other posts with my thoughts will be added here as they’re posted.

* This year there was a third Andy, and her name was Rachel.


Here are links to the other post(s) in this series: